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15 Pro Athletes Who Joined the Enemy

by: Esteban On  Tuesday, December 18, 2012

athletes who joined the enemy played on both sides of rivalry

It’s one thing when one of your favorite athletes leaves your team. It’s another thing altogether when he leaves and goes to your most hated enemy. However, that’s what happened last week when former Red Sox Nation favorite Kevin Youkilis agreed to a one-year, $12 million contract with the—gasp!—New York Yankees.

Sure, the Red Sox unceremoniously dumped Youk last season, so the guy certainly has no loyalties to the organization. In fact, he probably signed on with the Yanks for 2013 just to get a chance to run it in the Red Sox’s face. But to the fans, it’s different. Youkilis was beloved in Boston. Hell, he’s married to Tom Brady’s sister. Tom Freakin’ Brady. That made Youk Beantown royalty. And now he’s in pinstripes.

Anyway, in light of this development, I thought we’d see where Kevin Youkilis ranks among other athletes who ditched (or got ditched by) a team to play for their arch rivals. Curious? Then keep on clicking to see who’s here…


15. Jeff Kent

15 jeff kent dodgers - athletes who joined the enemy played on both sides of rivalry

Interestingly, Jeff Kent’s career didn’t take off until he started playing for San Francisco and got to bat in the #2 spot in the order right behind some guy named Barry Bonds. Funny how that works.

Anyway, Kent won the N.L. MVP Award in 2000 with a career-best line of .334/.424/.496 and 33 HRs. After the 2002 season (in which the Giants lost the World Series to the Angels), Kent and his mustache moved to Houton and played to seasons with the Astros before joining the Giants’ biggest rivals via free agency: the Los Angeles Dodgers.

Don’t believe these teams have a nasty rivalry going? Well, don’t tell that to the Giants fan who was nearly beaten to death outside Dodger Stadium on opening day in 2011.


14. Kevin Youkilis


Yep, Youkilis’ move to the Yankees only sits at #14. It’s not that this move didn’t grind the gears of Red Sox and Yankees fans alike. It did. It’s just that Youkilis doesn’t quite embody the essence of Red Sox-ness like some players have in the past—some players that we’ll soon see on this list.


13. Marian Hossa

13 marian hossa red wings - athletes who joined the enemy played on both sides of rivalry

Marion Hossa joined “the enemy” not once but twice.

The first time came right after his Pittsburgh Penguins lost to the Red Wings in the 2008 Stanley Cup Finals. Though Pittsburgh reportedly offered Hossa 5-year deal worth $7 million annually, the guy turned it down to sign a one-year deal with Detroit for $7.45 million. Why? Because he thought Detoit offered the best chance for him to win a Cup.

Obviously, that was admirable to impartial observers—a guy turning down a ton of money to win the Stanley Cup—but it burned the Penguins and their fans. So when Sid the Kid and company beat the Red Wings in Game 7 in Detroit the following year to bring the Cup to Pittsburgh, that victory tasted especially sweet.

But it doesn’t end there with Hossa. Oh no. After the 2009 season, Hossa then left the Red Wings for their greatest rival: the Chicago Blackhawks.

At least that time Hossa finally did win the Cup.


12. Guy Lafleur

12 guy lafleur nordiques - athletes who joined the enemy played on both sides of rivalry

Guy Lafleur is a Montreal Canadiens legend. He helped them win the Stanley Cup 5 times in the 1970s by scoring at least 50 goals and 100 points in six straight seasons. So when he retired in 1985, everyone thought he had retired a Canadien.

Then he came back in 1988. At first it wasn’t so terrible because it was with the Rangers. But after one season in New York he moved to the Quebec Nordiques.

Now, this one is tricky. On the one hand, at least Lafleur returned to his native Quebec. So that’s something. But, on the other hand, he returned to Quebec to play for a big Montreal Canadiens rival in the Nordiques. Sure, it could have been worse: Lafleur could have joined the Toronto Maple Leafs or the Boston Bruins. Either of those probably would have sparked riots in Montreal. But playing for the Nordiques still burned.

You see, in addition to a simple geographic rivalry, the Canadiens and Nordiques had an economic and political rivalry as well. The teams were owned by rival breweries (Molson owned the Canadiens while Carling O’Keefe owned the Nordiques) and their fan base generally was split along the lines of succession: most Canadiens fans were in favor of Quebec remaning part of Canada, while most Nordiques fans were in favor of Queben becoming an independent nation.

So, yeah, Lafleur playing for the Nordiques was a big deal.


11. Rod Woodson


Rod Woodson actually played on all sides of two different sets of heated NFL rivalries: Steelers-Ravens and Niners-Raiders. However, since he only spent one season in San Francisco, we’re just going to focus on the Steelers-Ravens thing.

You see, this Hall of Fame cornerback played 10 seasons in Pittsburgh, from 1987 to 1996, and he was an All-Pro in half of them. But when he became a free agent, the Steelers decided they couldn’t afford his asking price. (He was, after all, north of 30 years old and playing a defensive position that relies on speed and reflexes.) So he took his talents to the City by the Bay. And the breakup was painful for Steelers fans, but not that painful…until Woodson joined Ray Lewis and the Baltimore Ravens in 1998.

In case you somehow didn’t realize it, the Steelers and Ravens hate each other. They make up one of the most competitive and fierce rivalries in the NFL these days, and they have since the Ravens moved to Baltimore in 1996. So Hall of Fame Steeler Woodson to the Ravers? Wow, that hurt.



10. Terrell Owens


Terrell Owens started out in San Francisco. Then he moved to the Eagles as a free agent. And it was no big deal because the Niners and Eagles are huge rivals. But you know who are big rivals? The Niners and Cowboys. And the Eagles and Cowboys. And of course, sure enough, after just two seasons in Philly, T.O. got himself run out of town and he ended up in Dallas.

Seriously. A former 49er and former Eagle who stomped on the star on Dallas’ field as a sign of disrespect became a Cowboy.

I think this one actually hurt Cowboys fans more than it hurt Eagles or 49ers fans.


9. Johnny Damon

9 johnny damon - athletes who joined the enemy played on both sides of rivalry

Johnny Damon was part of those so-called “idiots” in Boston who finally, improbably, magically ended the “Curse of the Bambino” in 2004 by winning the World Series. So he and pretty much everyone else on that team was immediate Red Sox royalty for life.

But then Johnn Damon cut his long locks, shaved his caveman beard, and signed as a free agent with the f#$!ing Yankees. So, um, so much for being Boston Royalty.


8. Chris Chelios

8 chris chelios red wings - athletes who joined the enemy played on both sides of rivalry

Chelios grew up in Chicago. Rooting for the Blackhawks. Then he played for the Blackhawks. And he won Norris Trophies. And led them to the Stanley Cup finals. It was perfect. But then the Blackhawks traded Chelios to their oldest and most hated rival: the Detroit Red Wings. It was almost unthinkable. Grown men wept. Then the Red Wings won two Stanley Cups. He played until he was 48. Oops.

7. Jerry Rice


Man, at least Joe Montana went to the Chiefs when the 49ers ended their epic quarterback controversy by replacing him with Steve Young. But Jerry Rice? The greatest receiver of all-time? He just went across the Bay to Oakland.

That was cold, Jerry.


6. Deion Sanders

6 deion sanders redskins - athletes who joined the enemy played on both sides of rivalry

Neon Deon started out with Atlanta and made a stop in San Francisco before heading to Dallas. But once he was there, with the Cowboys, it seemed like he’d be there forever. He was now a true superstar.

Then in 2000, Deion Sanders left the Cowboys to play for their most hated rival: the Washington Redskins. It was just unthinkable.


5. Shaquille O'Neal

5 shaquille o'neal celtics - athletes who joined the enemy played on both sides of rivalry

Shaq bounced around a lot in the twilight of his career, but his stints in Miami, Cleveland, Phoenix weren’t that big of a deal. What was a big deal was the last stop on his farewell tour of the NBA: Boston. I mean, seriously, a guy who was part of a Lakers dynasty singing up to play for the Celtics? Could you imagine Magic or Kareem or Kobe doing that? (Answer: no.)


4. Figo

4 figo real madrid - athletes who joined the enemy played on both sides of rivalry

Huge “transfers” (as they call player transacts in soccer) aren’t that big of a deal. They happens all the time. Beckham played with Man U. Then he played with Real. Balotelli played for Inter Milan. Now he plays for Man City. People have their feeling hurt, but they get over it.

However, when Portuguese superstar Figo left Barcelona for Real Madrid in 2000 people went ape sh-t. This of course is because Barcelona and Real Madrid have one of the biggest rivalries in all of sports. It would be like the Yankees and Red Sox if a fascist dictator had been a Yankees fan and brutally suppressed the people of Boston. (Google “Francisco Franco.”)

So when Figo went to Madrid, he became enemy #1 one in Barcelona. And when he visited Camp Nou, fans threw all sorts of stuff at him…including, on one occasion, a pig’s head.


3. Roger Clemens


The Boston Red Sox tried to re-sign the best pitcher in baseball after the 1996 season. Or at least they said they did. But Clemens wasn’t happy with what they were offering, so he signed with the interdivisional rival Toronto Blue Jays. That was bad. But it got so, so much worse.

After winning two Cy Young Awards with Toronto in 1997 and 1998 (thanks, steroids!), Clemens wanted out of Toronto. So the Jays traded the legendary jerk to the Yankees, thus thrusting the knife the rest of the way into the heart of Red Sox Nation.


2. Brett Favre


It was time for Brett Favre to leave Green Bay in 2007. Packers fans were hoping he would just retire, and thus remain a Packer for life. But that didn’t happen. Instead, Favre went to the New York Jets. But hey, it could have been worse. Favre could have gone to a division rival like the Vikings.

Wait, what!?!? Favre did go to the Vikings in 2009? What, was he trying to rub it in or something?


1. Wade Boggs

1 wade boggs yankees - athletes who joined the enemy played on both sides of rivalry

There are some players who simply are Red Sox, players adopted and beloved so thoroughly by the city of Boston that the idea of them playing anywhere else is unthinkable.

Ted Williams was one of these players. So was the great Carl Yastrzemski. And so was Wade Boggs.

Boggs won the A.L. batting title 5 times with the Red Sox and the Silver Slugger (for the best hitter at his position, third base) 6 times. And of course, he was a perennial All-Star, too, having made 8 straight appearances as a Red Sox from 1985 to 1992.

But after 1992, the Boston management thought Boggs, then 34, was starting to lose it. So they decided not to sign him. And that, of course, is how Wade Boggs became a New York Yankee.

In 1993 and 1994, Boggs won two more batting titles. Then, in 1996, he finally won a World Series—only it was in pin stripes. And Boston wept.